Al-Qadisiyah University

College of Pharmacy

‫إعداد الطلبة‬
‫علي عبد الحسين عبادي‬
‫رسل عادل حليم‬
‫اسيل فرحان عبود‬

Determination of ‫زهراء سلطان كاظم‬

‫مريم عطية فرحان‬

Solubility Class ‫رسل محسن كاظم‬

‫براء جواد عبد الكاظم‬

Company ‫ فرات عادل جندي‬1

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(Group B3)
 Determination of Solubility Class 1
1- Introduction:
Solubility is the extent to which a compound, called the solute, dissolves in a
liquid, called the solvent. In dissolving a compound, the energy needed to break up
the interactions between the molecules or ions of the solute comes from new
interactions between the solute and the solvent.

Compounds dissolve in solvents having similar kinds of intermolecular forces.

Water and organic liquids are two different kinds of solvents. Water is very polar
because it is capable of hydrogen bonding with a solute. Many organic solvents are
either nonpolar, like carbon tetrachloride (CCl4) and hexane [CH3(CH2)4CH3], or
weakly polar like diethyl ether (CH3CH2OCH2CH3).
Ionic compounds are held together by strong electrostatic forces, so they need very
polar solvents to dissolve. Most ionic compounds are soluble in water, but are
insoluble in organic solvents. To dissolve an ionic compound, the strong ion-ion
interactions must be replaced by many weaker ion-dipole interactions.
Most organic compounds are soluble in organic solvents (remember, like dissolves
like). An organic compound is water soluble only if it contains one polar
functional group capable of hydrogen bonding with the solvent for every five C
atoms it contains. In other words, a water-soluble organic compound has an O- or
N-containing functional group that solubilizes its nonpolar carbon backbone.
Compare, for example, the solubility of butane and acetone in H 2O and CCl4.
Determination of Solubility Class 2

Because butane and acetone are both organic compounds having a C- C and C- H
backbone, they are soluble in the organic solvent CCl 4. Butane, a nonpolar molecule,
is insoluble in the polar solvent H 2O. Acetone, however, is H2O soluble because it
contains only three C atoms and its O atom can hydrogen bond with one H atom of
H2O. In fact, acetone is so soluble in water that acetone and water are miscible-they
form solutions in all proportions with each other.

The size of an organic molecule with a polar functional group determines its water
solubility. A low molecular weight alcohol like ethanol is water soluble because it
has a small carbon skeleton (≤ five C atoms) compared to the size of its polar OH
group. Cholesterol, on the other hand, has 27 carbon atoms and only one OH group.
 Determination of Solubility Class 3
Its carbon skeleton is too large for the OH group to solubilize by hydrogen bonding,
so cholesterol is insoluble in water.

Table 1: Solubility summary

Example about Table 1: Which compounds are water soluble?

▪ A has five C atoms and a polar C-Cl bond, but it is incapable of hydrogen bonding
with H2O, making it H2O insoluble.

▪ B has five C atoms and a polar OH group able to hydrogen bond to H 2O, making
it H2O soluble.

2- Purpose of the experiment:

In this experiment we begin the process of determining the structural composition of
organic compounds based upon interpretation of simple solubility tests can be
extremely useful in organic structure determination.
 Determination of Solubility Class 4
3- Equipment:
▪ 10 mL graduated cylinder.
▪ 6-10 test tubes, test tube rack.
▪ pH paper.
▪ Spatula.
▪ Pasteur pipet, with latex bulb.
▪ Transfer pipet.

4- Procedure:
1. Water Solubility. Place 0.05 mL or 25 mg of compound in a small test tube, and
add 0.75 mL of water in small portions. Shake test tube vigorously after the
addition of each portion of solvent. If water soluble, go on to step 2; otherwise
proceed to step 3.

2. Ether Solubility. Place 0.05 mL or 25 mg of compound in a small test tube, and

add 0.75 mL of diethyl ether in small portions. Shake test tube vigorously after
the addition of each portion of solvent. If the compound is both water and ether
soluble, the acid-base properties of the compound should be determined with
litmus.

▪ litmus turns red - water soluble acidic compound (class Sa)

▪ litmus turns blue - water soluble basic compound (class Sb)
▪ litmus neutral - water soluble general compound (class Sg)

If the compound is not ether soluble it is a salt, amino acid, or contains many
hydrophilic functionalities (class S)

3. 5% NaOH Solubility. Place 0.05 mL or 25 mg of compound in a small test tube,

and add 0.75 mL of NaOH solution in small portions. Shake test tube vigorously
after the addition of each portion of solvent. If NaOH soluble, go on to step 4;
otherwise proceed to step 5.

4. 5% NaHCO3 Solubility. Place 0.05 mL or 25 mg of compound in a small test

tube, and add 0.75 mL of NaHCO3 solution in small portions. Shake test tube
vigorously after the addition of each portion of solvent. If NaHCO 3 soluble, then
it is a strong organic acid (class As). If not NaHCO3 soluble, then it is a weak
organic acid (class Aw).

5. 5% HCl Solubility. Place 0.05 mL or 25 mg of compound in a small test tube,

and add 0.75 mL of HCl solution in small portions. Shake test tube vigorously
 Determination of Solubility Class 5
after the addition of each portion of solvent. If HCl soluble, then it is an organic
base (class B). If not HCl soluble, then go on to step 6.

6. 96% H2SO4 Solubility. Place 0.6 mL of H2SO4 in a small test tube, and add 0.05
mL or 25 mg of compound. Shake test tube vigorously. If H 2SO4 soluble, then it
is a neutral compound (class N). If not H2SO4 soluble, then it is an inert compound
(class I).

Figure 1: Solubility test flow chart

5- Dissection:
5.1- Water Solubility:
Water is a polar solvent with a dielectric constant equal to 80. It has the ability to
form hydrogen bonding and can act either as an acid or a base. Therefore, it can
dissolve:
▪ Salts of ammonium ion (RNH4+) or organic acids salts with alkali metal cations
(RCOO-).
▪ Ionic compounds.
 Determination of Solubility Class 6
▪ Polar compounds “like dissolves like”.
▪ Organic compounds with low molecular weight (less than 5 carbon atoms) such
as alcohols, aldehydes, ketones, and carboxylic acids.

Water is useful to determine the degree of acidity of a compound, even if the

compound is insoluble in water, using litmus paper (acidic, basic, or neutral).

5.2- Ether:
Ether is a non-polar solvent having a dielectric constant of 4.3. It cannot form
hydrogen bonding (unassociated liquid). Therefore, it differs from water in that it
cannot dissolve ionic compounds such as salts. It dissolves most water insoluble
compounds; therefore, in the determination of solubility class, the importance of
ether is for water soluble compounds only and no further solubility tests using the
remaining solvents are to be done.
Accordingly, two probabilities are there:

1. Compounds soluble in both water and ether. These compounds:

▪ are non-ionic.
▪ contain five or less carbon atoms.
▪ contain an active group that is polar and can form hydrogen bonding.
▪ contain only one strong polar group.

This division of compounds includes aldehydes, ketenes, and aliphatic acids.

2. Compounds soluble in water only (but not in ether). These compounds:

▪ are ionic.
▪ contain two or more polar groups with no more than four carbon atoms per
each polar group.

This group includes ionic salts such as salts of carboxylic acids and amines and
compounds with more than one active group such as poly hydroxylated
compounds and carbohydrates.

5.3- 5% NaOH & 5% NaHCO3:

Water insoluble compounds must be tested first in 5% sodium hydroxide solution
which is a basic solvent. It reacts with water insoluble compounds that are capable
of donating protons such as strong and weak acids. The stronger the acid, the weaker
the base it can react with. Water insoluble compounds that dissolve in 5% sodium
hydroxide solution must also be tested for solubility in 5% sodium bicarbonate
solution. Therefore, for water insoluble acidic compounds sodium hydroxide
 Determination of Solubility Class 7
solution is considered as a detecting solvent whereas sodium bicarbonate solution is
called as a sub classifying solvent since it can react with strong acids only. That is,
these two solvents give an idea about the acidity degree of the compound.
Two probabilities are there:

1. Compounds soluble in both bases. This class includes strong acids that have the
ability to react with weak bases (carboxylic acids) and phenols with electron
withdrawing groups (e.g., -NO2). Protons are weakly attached and can be given
easily.

2. Compounds soluble in 5% sodium hydroxide solution only. This group

includes phenols, amides, and amino acids (weak acids).

5.4- 5% HCl:
If the compound is insoluble in water and sodium hydroxide solution (and, hence,
insoluble in sodium bicarbonate solution too), this means that the compound is not
an acid but, rather, is either a basic compound or a neutral compound. 5%
hydrochloric acid solution, which can dissolve basic compounds such as amines
(RNH2), is used for such a compound. If the compound is soluble in this solvent,
then it is from class that includes primary, secondary, and tertiary amines.

5.5- 96% H2SO4:

If the compound is insoluble in water, 5% sodium hydroxide solution, and 5%
hydrochloric acid solution, solubility in cold concentrated sulfuric acid should be
tested. If the compound is soluble in this acid, it belongs to class which includes
neutral compounds such as high molecular weight alcohols, aldehydes, ketones,
esters, and ethers (more than four carbon atoms), and unsaturated hydrocarbons. On
the other hand, compounds that are insoluble in cold concentrated sulfuric acid
belong to class which includes inert aliphatic (saturated) hydrocarbons, aromatic
hydrocarbons, haloalkanes, and aryl halides.
 Determination of Solubility Class 8
Reference:
[1] Janice Gorzynski Smith, “Organic Chemistry”, third edition, (2011).

[2] Azhar M. Jasim, Duraid H. Mohammad, “A Laboratory Manual on Practical

Organic Chemistry for 2nd year students”, (2012).